Jr for the past couple of weeks has been extra "whiny" Nothing is wrong health wise. But for example I was up at 11:30 last night and I would take him out roughly every 30 minutes because he was whiny and still up. (Not his normal I need the bathroom signal) I took him outside plenty of times between 8 and almost midnight. But when I'd take him outside, he and Sunshine (she follows him everywhere) would just wait by the door sometimes scratching the door to come back in. It felt like he was playing a "game" by taking him in and out.
Also at 6 in the morning he's already ready to get up and go outside which is fine during the week but on the weekends its not cool. But because I take him out early during the week. He expects to be taken out the same time on Saturday and Sunday. And he definitely doesn't "need" to go to the bathroom at that time as he was the same dog who would wait until I'd get up out of bed to take hime out.
I don't know why he's become like this I'm wondering if he wants to be an "outside" dog as he constantly seems to want out. Are yard is safe enough for that as we've had "outside" dogs before long term. But I also have a feeling he wouldn't "want" me to leave him out there all night once he realizes he'll stay out there all night.
Another thing is that maybe I'm "giving" in too much. Maybe I should stop taking him in and out constantly and just let him whine it out. For example just right not I put him in at 12 and and 1:20 he wanted to go back outside.
This is only a problem on Saturday and Sundays as I'm really not here during the week between 7AM to 5PM. I wonder if it could be because he wants "attention" as to be honest I haven't really "played" with him in a while. Also maybe tiring him out would help as in he loves to play fetch in the yard.

Try playing ball with him before bedtime. Then I would tell him 'not time yet' every time he tried to wake you up in the am's. May take time, but don't give in to him. On the other hand (playing devils advocate here) most dogs want to keep the same schedule they have during the week. I would NOT leave him outside all night. Also I might just pay more attention to him period. My dogs go to bed in their pens at 9pm and I get them up about 8-9 am. They get a treat before bed. They know they don't get out before I get up. Thank goodness for pens!

It's a bit hard to play with him ball before bedtime (my schedule and the other 2 dogs) but I literally just got inside from playing ball with him. I didn't want to over do it as he just ate. But he did get a good run and a pant. Although there's really no point as I don't have issues during the week. But its a way to give him more attention overall.
Talking to him makes it worse I've tried. I can tell him "shhh" but that's about it.
Lately on weekends I "give in" at about 7:40ish
I know it must be hard for him because during the week I take them out at 6:20 but its because I pretty much need to and I can't take them out any later. But lately it seems it's become more of an issue.
He sleeps in his crate but he sleeps inside my room. So he starts whining at about 6 and even worse when he sees me "move" Which is why I sleep on the other side of the bed next to Buddy Bear on the weekends as it seems to help.
I don't want to leave him outside but it's almost like he just constantly wants out. Today though after I took him to the front yard at about 1:20 I put him back in his crate and did a couple of things. Walked back in the room and he did get up but I just laid down and took a nap until 5 and he didn't whine to wake me up. I took him out as soon as I woke up. But I put on calming music which I'm not sure if it "really" helps the dogs but it definitely helps me feel calm.

YES music does help a lot. Research has shown that classical music does help to calm shelter dogs. Attention is always helpful too. Maybe you could play with him inside, just before bedtime? Especially on the weekend.

I am so lucky. Since my dogs were raised in their pens and have everything they need they don't wake me up. I need to get up to feed them, but they still don't bark to wake me. The little one 'groans' and wakes me up!! Today after a bad night, I didn't wake up until 9:20 am!!

That does sound like a nice setup as everything they need is basically available to them. I also had a bad night last night as it was later then midnight and couldn't fall asleep (thanks to anxiety)
Overall it be better to play with him ball outside as my dogs don't really get to roam the house freely. I didn't notice much of a difference last night he behaved the same way. Since he was a puppy he has always waited for me to go to "sleep" basically I'm in bed but watching a movie for example. It's also not necessarily on the TV either. It can be on my phone with earphones in. And he'll take short naps but will "watch" me to see that I'm still awake. He knows that once I put the phone down and ear plugs out I will most likely go to bed. Then he'll wait a bit and then goes to sleep himself. I wonder if that has to do with anything since he feels so close to me. It's like he waits to go to sleep with me. Which I find a bit weird as none of my other dogs do that.

I think you hit the nail on the head, so to speak. Where ever you want to play ball is fine. Attention is what is needed.

None of my chi's sleep in my room at night. The first night, they are in a carrier in my bed, but from there on they are in their pen. Not much problem with crying. This last pup I had to hide and then throw a shoe AT the pen (not in it). She got the idea quickly. Only did it once.

Yes, I think you may be right I definitely need to give him more attention.
Jr has slept probably only twice in the living room away from me and he had cried all night. So he absolutely needs to sleep in my room.